Director, People Operations and Technology at Pie Insurance

United States

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Not SpecifiedCompensation

Expert & Leadership (9+ years)Experience Level

Full TimeJob Type

UnknownVisa

Insurance, TechnologyIndustries

Requirements

Strategic leadership experience in people operations and technology, including multi-year strategy development and alignment with company objectives
Expertise in managing HR technology stacks, particularly Workday configuration, maintenance, and data integrity
Proven track record in people operations functions such as Tier 1 team member support, payroll management, workflow/process design, SOP management, reporting, analytics, and compliance
Experience partnering with Talent Operations and supporting post-hire team member lifecycle delivery and experience
Ability to provide structure, data, and analysis to support leaders and People Talent teams
Strong cross-functional collaboration skills with stakeholders including Finance & Accounting, Enterprise Technology, Internal Communications, Legal & Compliance, Product, Executive Team, Senior Leadership Team, and Office of the CEO
Proficiency in leveraging AI, technology, and business/people-centered approaches to elevate HR functions
Experience in a scaling organization (e.g., ~350 team members) with a focus on innovative, effective, and inclusive work culture

Responsibilities

Own post-hire team member lifecycle delivery and experience, providing structure, data, and analysis for Pie’s leaders and People Talent teams
Develop multi-year strategies for people operations and technology, co-developed with the CPO and executed via a multi-year roadmap
Lead people operations functions including Tier 1 support, payroll, People/Talent tech stack management (focus on Workday), workflow/process design, SOP management, reporting/analytics, and compliance
Directly manage the People Operations team (currently 3 full-time members), including development, coaching, training, performance management, and future team growth
Lead and develop new People team leaders to build bench strength
Establish and maintain collaborative relationships across the organization with key stakeholders (Finance, Enterprise Tech, Internal Comms, Legal/Compliance, Product, Exec/Senior Leadership, Office of the CEO)
Partner with People Partners, Total Rewards, Talent, and Executive Support/Space teams on strategy and execution
Serve in lead execution, supporting, and consultative roles on cross-functional projects using Pie’s Collaboration and Decision Making Framework
Ensure an innovative, effective, and inclusive work culture to retain and grow talent
Partner closely with Dir, Talent to support Talent Operations at the outset

Skills

Key technologies and capabilities for this role

AIHR TechnologyPeople OperationsPayrollData AnalysisBusiness IntelligenceAnalyticsStrategic Planning

Questions & Answers

Common questions about this position

What team does this role manage?

The role directly manages the People Operations team, currently comprised of three full-time team members with varying levels of experience and responsibility.

What is the reporting structure for the Director of People Operations and Technology?

The role reports to the Chief People Officer (CPO) and serves as a critical member of the People, Talent & Executive Support (PTE) leadership team.

What are the key responsibilities of this position?

The role owns post-hire team member lifecycle delivery, people operations and tech strategy, Tier 1 support, payroll, Workday management, workflows, reporting, analytics, compliance, and partners with Talent Operations.

What is the company size and culture like?

Pie has approximately 350 team members and is a diverse team of builders, dreamers, and entrepreneurs driven by core values and operating principles, emphasizing an innovative, effective, and inclusive work culture.

Is this role remote or office-based?

This information is not specified in the job description.

Pie Insurance

Provides workers' compensation insurance for small businesses

About Pie Insurance

Pie Insurance provides workers' compensation insurance specifically designed for small businesses. This type of insurance helps cover wage replacement and medical benefits for employees who are injured while working. The company utilizes data-driven technology to offer competitive pricing and ensure that clients receive quality coverage. The process for obtaining insurance quotes is quick and user-friendly, taking only three minutes, which is particularly beneficial for small business owners who may not have the time to deal with complicated insurance procedures. Pie Insurance operates in 38 states and Washington, D.C., with plans for further expansion. The company aims to deliver trusted and efficient insurance services, promising potential savings of up to 30% on workers' compensation insurance. Its unique approach lies in leveraging technology to simplify the insurance process, making it easier and more affordable for small businesses.

Washington, District of ColumbiaHeadquarters

2017Year Founded

$603.4MTotal Funding

SERIES_DCompany Stage

Fintech, Financial ServicesIndustries

201-500Employees